CN106432378B - Polyaminoalkyl glucoside and preparation method and application thereof - Google Patents
Polyaminoalkyl glucoside and preparation method and application thereof Download PDFInfo
- Publication number
- CN106432378B CN106432378B CN201510486574.9A CN201510486574A CN106432378B CN 106432378 B CN106432378 B CN 106432378B CN 201510486574 A CN201510486574 A CN 201510486574A CN 106432378 B CN106432378 B CN 106432378B
- Authority
- CN
- China
- Prior art keywords
- glycoside
- poly
- formula
- alkyl glycoside
- acid
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Active
Links
Landscapes
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The invention provides a poly (amino alkyl) glycoside, which has a structure shown in a formula I; in the formula I, R1Selected from alkyl with 1-10 carbon atoms; r2Selected from alkyl with 1-5 carbon atoms, m is 1-3, and n is 0-4. The invention provides a preparation method of the poly amino alkyl glycoside in the technical scheme, which comprises the following steps: reacting alkyl glycoside, an alkylene oxide compound, a chlorinating agent and an acid catalyst to obtain an intermediate product; and reacting the intermediate product with water and organic amine to obtain the poly-amino alkyl glycoside. The poly-amino alkyl glycoside provided by the invention has better shale inhibition and high temperature resistance. In addition, the poly-amino alkyl glycoside provided by the invention has better compatibility with drilling fluid. The poly-amino alkyl glycoside provided by the invention can be applied to drilling fluid, and is suitable for drilling construction of easily collapsed strata such as strong water-sensitive shale and shale-containing rock and shale gas horizontal wells.
Description
Technical Field
The invention relates to the technical field of alkyl glycoside, in particular to poly-amino alkyl glycoside and a preparation method and application thereof.
Background
In recent years, with the increasing number of deep wells, ultra-deep wells, highly deviated wells and horizontal wells in the field of oil drilling, the problem of borehole wall instability during drilling of deep-layer highly water-sensitive shale, mudstone-containing formations and other easily collapsed formations with high formation temperature in the deep wells and the ultra-deep wells cannot be solved well. The problem of borehole wall instability can be solved to a certain extent by adopting the oil-based drilling fluid, but the oil-based drilling fluid has the problems of high preparation cost and poor environmental protection performance; the amino strong inhibitor is used as a core main agent and is matched with other treating agents to prepare the water-based drilling fluid with better inhibition performance, the water-based drilling fluid has the performance of oil-based drilling fluid, but the amino strong inhibitor and other treating agents have poor compatibility, so that the control of the water-based drilling fluid in the aspect of stability has greater difficulty, and the popularization and the use of the water-based drilling fluid are limited.
The alkyl glycoside oil-based drilling fluid is provided abroad in the 90 th 20 th century, has better environmental protection performance, but because the inhibition performance and the high temperature resistance of the alkyl glycoside are poorer, more than 35 percent of alkyl glycoside needs to be added into the alkyl glycoside oil-based drilling fluid to fully exert the inhibition performance, the production cost of the drilling fluid is increased, and the popularization and the application of the drilling fluid are limited.
In order to overcome the defects of insufficient inhibition and high temperature resistance of alkyl glycoside, the structure of alkyl glycoside can be modified or optimized, functional groups with specific properties are introduced, and the preparation of alkyl glycoside derivatives with strong inhibition and good high temperature resistance becomes a research hotspot. At present, no compound of the poly-amino alkyl glycoside is reported.
Disclosure of Invention
In view of the above, the present invention aims to provide a poly (aminoalkyl) glycoside, and a preparation method and an application thereof, and the poly (aminoalkyl) glycoside provided by the present invention has good shale inhibition and high temperature resistance.
The invention provides a poly (aminoalkyl) glycoside having a structure represented by formula I:
in the formula I, R1Selected from alkyl with 1-10 carbon atoms;
R2selected from alkyl with 1-5 carbon atoms;
m is 1-3;
n is 0 to 4.
Preferably, in the formula I, R1Is methyl, ethyl, propyl, butyl, pentyl or hexyl;
R2is methyl, ethyl or propyl.
The poly-amino alkyl glycoside provided by the invention introduces organic polyamine into alkyl glycoside, and the poly-amino alkyl glycoside has better shale inhibition performance and high temperature resistance. Experimental results show that when the aqueous solution of the poly (aminoalkyl) glucoside with the mass concentration of 1% rolls for 16 hours at 180 ℃, the primary recovery rate of shale is more than 95%, and the relative recovery rate of shale is more than 98%; rolling for 16 hours at 300 ℃, wherein the primary recovery rate of the shale is more than 93 percent, and the relative recovery rate of the shale is more than 99 percent.
In addition, the poly-amino alkyl glycoside provided by the invention has better compatibility with drilling fluid. Experimental results show that 3% of the poly-amino alkyl glycoside provided by the invention is added into various drilling fluids, so that the performance of the drilling fluids is not damaged, the fluidity of the drilling fluids can be improved, the viscosity is reduced, the shear strength is improved, and the amount of filtrate invading stratum is reduced.
The invention provides a preparation method of the poly amino alkyl glycoside in the technical scheme, which comprises the following steps:
reacting alkyl glycoside, an alkylene oxide compound, a chlorinating agent and an acid catalyst to obtain an intermediate product, wherein the alkyl glycoside has a structure shown in a formula II:
in the formula II, R1Selected from alkyl with 1-10 carbon atoms;
the alkylene oxide compound has a structure shown in formula III:
in the formula III, R2Is an alkyl group having 1 to 5 carbon atoms;
reacting the intermediate product with water and organic amine to obtain poly-amino alkyl glycoside, wherein the organic amine has a structure shown in a formula IV:
in the formula IV, n is 0-4.
Preferably, the mass ratio of the alkyl glycoside to the alkylene oxide compound to the water to the acidic catalyst to the chlorinating agent to the organic amine is (10-15): (8-12): 50-90): 0.8-1.6): 9-11): 10-12.
Preferably, the alkyl glycoside is methyl glycoside, ethyl glycoside, propyl glycoside, butyl glycoside, pentyl glycoside or hexyl glycoside.
Preferably, the alkylene oxide is propylene oxide, butylene oxide or pentylene oxide.
Preferably, the acidic catalyst is hydrofluoric acid, hydrochloric acid, sulfuric acid, phosphoric acid, tartaric acid, oxalic acid, p-toluenesulfonic acid, dodecylbenzenesulfonic acid or sulfamic acid.
Preferably, the chlorinating agent is thionyl chloride, sulfuryl chloride, phosphorus trichloride or phosphorus pentachloride.
Preferably, the organic amine includes diethylenetriamine, triethylenetetramine, tetraethylenepentamine or pentaethylenehexamine.
The poly-amino alkyl glycoside prepared by the method provided by the invention has better shale inhibition performance and high temperature resistance. In addition, the poly-amino alkyl glycoside prepared by the method has better compatibility with drilling fluid. In addition, the preparation method of the poly-amino alkyl glycoside provided by the invention takes natural renewable substances as raw materials, and the prepared product is safe and environment-friendly; in addition, the reaction conditions in the preparation process are mild, the preparation process is simple, water is used as a solvent, and no wastewater, waste gas or waste residue is discharged in the production process.
The invention provides application of poly (amino alkyl glycoside) in drilling fluid, wherein the poly (amino alkyl glycoside) is the poly (amino alkyl glycoside) in the technical scheme or prepared by the method in the technical scheme.
In the invention, the polyamino alkyl glycoside has better shale inhibition and high temperature resistance, and the polyamino alkyl glycoside and the drilling fluid have better compatibility, the polyamino alkyl glycoside can be applied to the drilling fluid, and the addition of the polyamino alkyl glycoside into the drilling fluid can improve the shale inhibition and high temperature resistance of the drilling fluid, so that the drilling fluid is suitable for drilling construction of high water sensitivity shale, shale containing shale and other easily collapsed strata and shale gas horizontal wells.
Detailed Description
The technical solutions in the embodiments of the present invention will be clearly and completely described below, and it is obvious that the described embodiments are only a part of the embodiments of the present invention, and not all embodiments. All other embodiments, which can be derived by a person skilled in the art from the embodiments given herein without making any creative effort, shall fall within the protection scope of the present invention.
The invention provides a poly (aminoalkyl) glycoside having a structure represented by formula I:
in the formula I, R1Selected from alkyl with 1-10 carbon atoms;
R2selected from alkyl with 1-5 carbon atoms;
m is 1-3;
n is 0 to 4.
In the embodiment of the invention, R in the formula I1Is methyl, ethyl, propyl, butyl, pentyl or hexyl. In the embodiment of the invention, R in the formula I2Is methyl, ethyl or propyl. In an embodiment of the invention, the number average molecular weight of the polyaminoalkyl glycoside is 300-600; in other embodiments, the number average molecular weight of the polyaminoalkyl glycoside is 350 to 550; in another embodiment, the number average molecular weight of the polyaminoalkyl glycoside is 400 to 500. The organic polyamine is introduced into the alkyl glycoside in the poly-amino alkyl glycoside provided by the invention, and the poly-amino alkyl glycoside has better shale inhibition and high temperature resistance. In addition, the poly-amino alkyl glycoside provided by the invention has better compatibility with drilling fluid.
The invention provides a preparation method of the poly amino alkyl glycoside in the technical scheme, which comprises the following steps:
reacting alkyl glycoside, an alkylene oxide compound, a chlorinating agent and an acid catalyst to obtain an intermediate product, wherein the alkyl glycoside has a structure shown in a formula II:
in the formula II, R1Selected from alkyl with 1-10 carbon atoms;
the alkylene oxide compound has a structure shown in formula III:
in the formula III, R2Is an alkyl group having 1 to 5 carbon atoms;
reacting the intermediate product with water and organic amine to obtain poly-amino alkyl glycoside, wherein the organic amine has a structure shown in a formula IV:
in the formula IV, n is 0-4.
In the embodiment of the invention, the reaction temperature of the alkyl glycoside, the alkylene oxide compound, the chlorinating agent and the acid catalyst is 40-80 ℃; in other embodiments, the reaction temperature of the alkyl glycoside, the alkylene oxide, the chlorinating agent, and the acidic catalyst is from 50 ℃ to 70 ℃. In the embodiment of the invention, the reaction time of the alkyl glycoside, the alkylene oxide compound, the chlorinating agent and the acid catalyst is 0.5-3 hours; in other embodiments, the reaction time of the alkyl glycoside, the alkylene oxide, the chlorinating agent, and the acidic catalyst is 1 hour to 2 hours. In the embodiment of the invention, the reaction pressure of the alkyl glycoside, the alkylene oxide compound, the chlorinating agent and the acid catalyst is 1 MPa-5 MPa; in other embodiments, the reaction pressure of the alkyl glycoside, the alkylene oxide, the chlorinating agent and the acidic catalyst is 2MPa to 4 MPa. In the embodiment of the present invention, the alkyl glycoside, the alkylene oxide compound, the chlorinating agent and the acidic catalyst may be reacted with stirring.
After the intermediate product is obtained, the intermediate product is reacted with water and organic amine to obtain the poly-amino alkyl glycoside. In the embodiment of the invention, the temperature for the reaction of the intermediate product, water and organic amine is 180-240 ℃; in other embodiments, the temperature of the reaction of the intermediate product with water and the organic amine is from 200 ℃ to 220 ℃. In the embodiment of the invention, the reaction time of the intermediate product, water and organic amine is 2-4 hours; in other embodiments, the intermediate is reacted with water and the organic amine for a time period of 2.5 hours to 3.5 hours. In the embodiment of the present invention, the intermediate product may be reacted with water and organic amine under stirring.
In the embodiment of the invention, after the intermediate product is reacted with water and organic amine, the obtained reaction product is dried to remove water, and the poly-amino alkyl glycoside is obtained.
In the present invention, the alkyl glycoside has a structure represented by formula II, wherein R is represented by formula II1R is as defined in the above technical scheme1And the description is omitted here. In embodiments of the invention, the alkyl glycoside may be methyl glycoside, ethyl glycoside, propyl glycoside, butyl glycoside, pentyl glycoside or hexyl glycoside. In the invention, the alkylene oxide compound has a structure shown in a formula III, wherein R in the formula III2R in the technical scheme2And the description is omitted here. In embodiments of the present invention, the alkylene oxide compound may be propylene oxide, butylene oxide or pentylene oxide. In embodiments of the present invention, the acidic catalyst may be hydrofluoric acid, hydrochloric acid, sulfuric acid, phosphoric acid, tartaric acid, oxalic acid, p-toluenesulfonic acid, dodecylbenzenesulfonic acid, or sulfamic acid. In an embodiment of the present invention, the chlorinating agent may be thionyl chloride, sulfuryl chloride, phosphorus trichloride or phosphorus pentachloride. In the invention, the organic amine has a structure shown in formula IV, and n in formula IV is consistent with n in the technical scheme, which is not described herein again. In embodiments of the invention, the organic amine comprises ethylenediamine, diethylenetriamine, triethylenetetramine, tetraethylenepentamine or pentaethylenehexamine.
In the embodiment of the invention, the mass ratio of the alkyl glycoside, the alkylene oxide compound, the water, the acidic catalyst, the chlorinating agent and the organic amine is (10-15): 8-12): 50-90: (0.8-1.6): 9-11): 10-12; in other embodiments, the mass ratio of the alkyl glycoside, the alkylene oxide compound, the water, the acidic catalyst, the chlorinating agent and the organic amine is (11-14): 9-11): 60-80 ]: 1-1.4): 9.5-10.5): 10.5-11.5; in another embodiment, the mass ratio of the alkyl glycoside, the alkylene oxide compound, the water, the acidic catalyst, the chlorinating agent and the organic amine is (12-13): 9.5-10.5): 65-75): 1.2-1.4): 10: 11.
In the present invention, the poly (aminoalkyl glycoside) is identical to the poly (aminoalkyl glycoside) described in the above technical solution, and will not be described herein again.
The poly-amino alkyl glycoside prepared by the method provided by the invention has better shale inhibition performance and high temperature resistance. In addition, the poly-amino alkyl glycoside prepared by the method has better compatibility with drilling fluid. In addition, the preparation method of the poly-amino alkyl glycoside provided by the invention takes natural renewable substances as raw materials, and the prepared product is safe and environment-friendly; in addition, the reaction conditions in the preparation process are mild, the preparation process is simple, water is used as a solvent, and no wastewater, waste gas or waste residue is discharged in the production process.
The invention provides application of poly (amino alkyl glycoside) in drilling fluid, wherein the poly (amino alkyl glycoside) is the poly (amino alkyl glycoside) in the technical scheme or prepared by the method in the technical scheme.
In the present invention, the poly (aminoalkyl glycoside) is identical to the poly (aminoalkyl glycoside) described in the above technical solution, and is not described herein again. In the invention, the polyamino alkyl glycoside has better shale inhibition and high temperature resistance, and the polyamino alkyl glycoside and the drilling fluid have better compatibility, the polyamino alkyl glycoside can be applied to the drilling fluid, and the addition of the polyamino alkyl glycoside into the drilling fluid can improve the shale inhibition and high temperature resistance of the drilling fluid, so that the drilling fluid is suitable for drilling construction of high water sensitivity shale, shale containing shale and other easily collapsed strata and shale gas horizontal wells.
The poly (amino alkyl glycoside) provided by the invention is prepared into a poly (amino alkyl glycoside) aqueous solution with the mass concentration of 1%, the poly (amino alkyl glycoside) aqueous solution rolls at the high temperature of 180 ℃ and 300 ℃ for 16 hours respectively, and the shale primary recovery rate and the shale relative recovery rate are tested according to the following methods:
stirring the aqueous solution of the poly-amino alkyl glycoside with the mass concentration of 1% at 7000 rpm for 5min at a high speed, and pouring the aqueous solution of the poly-amino alkyl glycoside into an aging tank for later use; drying 2.0-5.0 mm of rock debris at 103 ℃ for 4h, and cooling to room temperature; weighing G0Placing the rock debris into an aging tank, rolling the rock debris and the poly-amino alkyl glycoside aqueous solution with the mass concentration of 1% at 180 ℃ or 300 ℃ for 16h, cooling, taking out, recovering the rock debris by using a sieve with the pore diameter of 0.42mm, drying at 103 ℃ for 4h, cooling to room temperature, weighing the mass of the recovered rock debris and recording as G1(ii) a Then putting the weighed and overweight recovered rock debris into clear water, rolling for 2 hours at 180 ℃ or 300 ℃, taking out after cooling, recovering the rock debris by using a sieve with the aperture of 0.42mm, drying for 4 hours at 103 ℃, cooling to room temperature, weighing the mass of the recovered rock debris, and recording as G2(ii) a Calculating the primary recovery rate, the secondary recovery rate and the relative recovery rate of the shale according to the following formulas:
primary recovery rate of shale1/G0×100％；
Shale secondary recovery rate G2/G0×100％；
The relative recovery rate of the shale is equal to the secondary recovery rate of the shale/the primary recovery rate of the shale multiplied by 100 percent;
the calculation result is that the aqueous solution of the poly-amino alkyl glycoside with the mass concentration of 1% rolls for 16 hours at the high temperature of 180 ℃, the primary recovery rate of the shale is more than 95%, and the relative recovery rate of the shale is more than 98%; rolling for 16h at the high temperature of 300 ℃, wherein the primary recovery rate of the shale is more than 93 percent, and the relative recovery rate of the shale is more than 99 percent.
The poly-amidoalkyl glucoside provided by the invention is respectively added into a soil-free phase drilling fluid, a low solid phase polymer drilling fluid and a polysulfonate drilling fluid, the addition amount is 3 percent of the mass of the drilling fluid, and the soil-free phase drilling fluid comprises 0.6 percent of xanthan gum, 0.4 percent of high-viscosity sodium carboxymethyl cellulose, 0.6 percent of low-methyl sodium cellulose, 3 percent of non-penetration plugging agent, 0.4 percent of NaOH and 0.2 percent of Na2CO324% of industrial salt and the balance of water; the low solid polymer drilling fluid comprises 0.3 mass percent of Na2CO30.5 to 1.0 percent of low-viscosity sodium carboxymethyl cellulose, 0.1 to 0.2 percent of tackifier 80A51, 0.3 to 1.0 percent of polymer fluid loss additive COP-LFL/HFL, 10 percent of crude oil and the balance of water; the polysulfonate drilling fluid comprises 4 percent of bentonite and 0.2 percent of Na in percentage by mass2CO30.2 percent of NaOH, 0.1 to 0.2 percent of tackifier 80A51, 0.5 to 1.0 percent of low-viscosity sodium carboxymethyl cellulose, 0.3 to 1.0 percent of polymer fluid loss additive COP-LFL/HFL, a proper amount of salt, 2 to 4 percent of sulfomethyl phenolic resin SMP and sulfonated lignite SMC, and the balance of water.
According to GB/T16783.1-2014, oil and gas industry drilling fluid field test part 1: the standard of water-based drilling fluid tests the apparent viscosity, plastic viscosity, dynamic shear force, static shear force, medium pressure filtration loss, density and pH value of the above soil-free drilling fluid and soil-free drilling fluid added with the polyamino alkyl glycoside, low solid polymer drilling fluid and low solid polymer drilling fluid added with the polyamino alkyl glycoside, polysulfonate drilling fluid and polysulfonate drilling fluid added with the polyamino alkyl glycoside.
The test result shows that the apparent viscosity of the soilless-phase drilling fluid is 48mPa.s, and the apparent viscosity of the soilless-phase drilling fluid added with the poly-amino alkyl glycoside is 57 to 58 mPa.s; the plastic viscosity is 22mPa.s, and the plastic viscosity of the soilless-phase drilling fluid added with the poly-amino alkyl glycoside is 26 mPa.s-27 mPa.s; the dynamic shear force is 26Pa, and the dynamic shear force of the soilless phase drilling fluid added with the poly-amino alkyl glucoside is 31 Pa-32 Pa; the static shear force is 10.0/13.5, and the static shear force of the soilless phase drilling fluid added with the poly-amino alkyl glycoside is 5.0-6.0/10.0; the medium pressure filtration loss is 6.0mL, and the medium pressure filtration loss of the soilless-phase drilling fluid added with the poly-amino alkyl glycoside is 5.6 mL-5.7 mL; the density was 1.14g/cm3The density of the soil-free phase drilling fluid added with the poly-amino alkyl glucoside is 1.15g/cm3～1.16g/cm3(ii) a The pH value is 8, and the pH value of the soilless phase drilling fluid added with the poly-amino alkyl glucoside is 9.
The apparent viscosity of the low solid phase polymer drilling fluid is 93mPa.s, and the apparent viscosity of the low solid phase polymer drilling fluid added with the poly-amino alkyl glycoside is 72 mPa.s-73 mPa.s; the plastic viscosity is 57mPa.s, and the plastic viscosity of the low solid-phase polymer drilling fluid added with the poly-amino alkyl glycoside is 58-59 mPa.s; the dynamic shear force is 36Pa, and the dynamic shear force of the low solid-phase polymer drilling fluid added with the poly-amino alkyl glycoside is 14 Pa-15 Pa; the static shear force is 15.0/20.0, and the static shear force of the low solid phase polymer drilling fluid added with the poly-amino alkyl glycoside is 2.0-3.0/8.0; the medium pressure filtration loss is 4.6mL, and the medium pressure filtration loss of the low solid phase polymer drilling fluid added with the poly-amino alkyl glycoside is 4.2 mL-4.3 mL; the density was 1.27g/cm3The density of the low solid polymer drilling fluid added with the poly-amino alkyl glucoside is 1.27g/cm3～1.28g/cm3(ii) a The pH value is 8, and the pH value of the low solid phase polymer drilling fluid added with the poly-amino alkyl glucoside is 9.
The apparent viscosity of the polysulfonate drilling fluid is 49.5mPa.s, and the apparent viscosity of the polysulfonate drilling fluid added with the poly-amino alkyl glycoside is 42 to 43 mPa.s; the plastic viscosity is 39mPa.s, and the plastic viscosity of the polysulfonate drilling fluid added with the poly-amino alkyl glycoside is 36 to 37 mPa.s; dynamic shear force is 10.5Pa, the dynamic shear force of the polysulfonate drilling fluid added with the poly-amino alkyl glycoside is 6Pa to 7 Pa; the static shear force is 4.5/23.5, and the static shear force of the polysulfonate drilling fluid added with the poly-amino alkyl glycoside is 2.0-3.0/8.0; the medium pressure filtration loss is 2.8mL, and the medium pressure filtration loss of the polysulfonate drilling fluid added with the poly-amino alkyl glycoside is 1.6 mL-1.7 mL; the density was 1.43g/cm3The density of the polysulfonic drilling fluid added with the poly-amino alkyl glycoside is 1.43g/cm3～1.44g/cm3(ii) a The pH value is 9, and the pH value of the polysulfonate drilling fluid added with the poly-amino alkyl glucoside is 9.
The starting materials used in the following examples of the present invention are all commercially available products.
Example 1
Adding 10g of methyl glycoside, 8g of propylene oxide, 9g of thionyl chloride and 0.8g of hydrofluoric acid into a high-temperature high-pressure reaction kettle, purging air in the kettle by using nitrogen, raising the pressure to 1.0MPa by using the nitrogen, starting stirring, raising the temperature to 40 ℃, and carrying out reaction for 0.5h to obtain an intermediate product;
adding 50g of water and 10g of ethylenediamine into the intermediate product, uniformly stirring and mixing, raising the temperature to 180 ℃, carrying out reaction for 2.0h, drying and removing water from the obtained reaction product to obtain the poly-amino methyl glycoside, wherein the yield is 95.67%.
The poly (aminomethyl) glycoside prepared in example 1 of the present invention has the structure shown in formula 1:
in the formula 1, m is 1-3.
According to the method of the technical scheme, the shale primary recovery rate and the shale relative recovery rate of the poly-amino-methyl-glycoside prepared in the embodiment 1 of the invention are tested when the poly-amino-methyl-glycoside rolls for 16 hours at 180 ℃, the test results are shown in table 1, and the table 1 is the shale inhibition performance test result of the poly-amino-alkyl-glycoside prepared in the embodiment of the invention.
According to the method of the technical scheme, the compatibility of the poly (amino alkyl glycoside) prepared in the embodiment 1 of the invention and the drilling fluid is tested, the test result is shown in table 2, and the table 2 is the test result of the compatibility of the poly (amino methyl glycoside) prepared in the embodiment 1 of the invention and the drilling fluid.
Example 2
Adding 11g of ethyl glucoside, 9g of epoxybutane, 10g of sulfuryl chloride and 0.9g of hydrochloric acid into a high-temperature high-pressure reaction kettle, purging air in the kettle by using nitrogen, raising the pressure to 2.0MPa by using the nitrogen, starting stirring, raising the temperature to 50 ℃, and carrying out reaction for 1 hour to obtain an intermediate product;
adding 55g of water and 10.5g of diethylenetriamine into the intermediate product, stirring and mixing uniformly, raising the temperature to 190 ℃, carrying out reaction for 3.0h, drying and removing water from the obtained reaction product to obtain the poly-amino ethyl glycoside, wherein the yield is 96.12%.
The poly (aminoethyl) glycoside prepared in example 2 of the present invention has the structure shown in formula 2:
in the formula 2, m is 1-3, and n is 1.
According to the method of the technical scheme, the shale recovery rate once and the shale relative recovery rate of the poly-aminoethyl glycoside prepared in the invention example 2 are tested after rolling for 16 hours at 180 ℃, and the test results are shown in table 1.
Example 3
Adding 12g of propyl glucoside, 10g of cyclopentane epoxide, 11g of phosphorus trichloride and 1.0g of sulfuric acid into a high-temperature high-pressure reaction kettle, purging air in the kettle by using nitrogen, raising the pressure to 3.0MPa by using the nitrogen, starting stirring, raising the temperature to 60 ℃, and carrying out reaction for 1.5 hours to obtain an intermediate product;
adding 60g of water and 11g of triethylene tetramine into the intermediate product, stirring and mixing uniformly, raising the temperature to 200 ℃, carrying out reaction for 4.0h, drying and removing water from the obtained reaction product to obtain the poly-aminopropyl glucoside, wherein the yield is 96.27%.
The poly (aminopropyl) glycoside prepared in example 3 of the present invention has the structure shown in formula 3:
in the formula 3, m is 1-3, and n is 2.
According to the method of the technical scheme, the shale recovery rate once and the shale relative recovery rate of the poly-aminopropyl glucoside prepared in the embodiment 3 of the invention rolling for 16 hours at 180 ℃ are tested, and the test results are shown in table 1.
Example 4
Adding 13g of butyl glucoside, 11g of propylene oxide, 11g of phosphorus pentachloride and 1.1g of phosphoric acid into a high-temperature high-pressure reaction kettle, purging air in the kettle by using nitrogen, raising the pressure to 4.0MPa by using the nitrogen, starting stirring, raising the temperature to 70 ℃, and carrying out reaction for 2 hours to obtain an intermediate product;
adding 65g of water and 11.5g of tetraethylenepentamine into the intermediate product, stirring and mixing uniformly, raising the temperature to 210 ℃, carrying out reaction for 2.0h, drying and removing water from the obtained reaction product to obtain the poly-amino butyl glucoside, wherein the yield is 95.38%.
The poly (aminobutylglucoside) prepared in example 4 of the present invention has a structure represented by formula 4:
in the formula 4, m is 1-3, and n is 3.
According to the method of the technical scheme, the shale recovery rate once and the shale relative recovery rate of the poly-amino butyl glucoside prepared in the embodiment 4 of the invention rolling for 16 hours at 180 ℃ are tested, and the test results are shown in table 1.
Example 5
Adding 14g of amyl glucoside, 12g of epoxybutane, 9g of thionyl chloride and 1.2g of tartaric acid into a high-temperature high-pressure reaction kettle, purging air in the kettle by using nitrogen, raising the pressure to 5.0MPa by using the nitrogen, starting stirring, raising the temperature to 80 ℃, and carrying out reaction for 2.5 hours to obtain an intermediate product;
adding 70g of water and 12g of pentaethylenehexamine into the intermediate product, stirring and mixing uniformly, raising the temperature to 220 ℃, carrying out reaction for 3.0h, drying and removing water from the obtained reaction product to obtain the poly-amino-pentyl-glucoside, wherein the yield is 95.84%.
The polyamino pentyl glycoside prepared in example 5 of the present invention has the structure shown in formula 5:
in the formula 5, m is 1-3, and n is 4.
According to the method of the above technical scheme, the shale recovery rate once and the shale relative recovery rate after the poly-amino amyl glycoside prepared in the invention example 5 rolls for 16 hours at 180 ℃ are tested, and the test results are shown in table 1.
Example 6
Adding 15g of hexyl glucoside, 12g of cyclopentane epoxide, 10g of sulfuryl chloride and 1.3g of oxalic acid into a high-temperature high-pressure reaction kettle, purging air in the kettle by nitrogen, raising the pressure to 5.0MPa by nitrogen, starting stirring, raising the temperature to 80 ℃, and carrying out reaction for 3 hours to obtain an intermediate product;
and adding 75g of water and 12g of diethylenetriamine into the intermediate product, uniformly stirring and mixing, raising the temperature to 240 ℃, carrying out reaction for 4.0h, drying and removing water from the obtained reaction product to obtain the poly (amino hexyl glucoside), wherein the yield is 95.19%.
The poly (amino hexyl glycoside) prepared in example 6 of the present invention has the structure shown in formula 6:
in the formula 6, m is 1-3, and n is 1.
According to the method of the technical scheme, the shale recovery rate once and the shale relative recovery rate of the poly-amino hexyl glucoside prepared by the invention in the embodiment 6 are tested after rolling for 16 hours at 180 ℃, and the test results are shown in the table 1.
Example 7
Adding 15g of methyl glycoside, 12g of propylene oxide, 11g of phosphorus trichloride and 1.4g of p-toluenesulfonic acid into a high-temperature high-pressure reaction kettle, purging air in the kettle by using nitrogen, raising the pressure to 5.0MPa by using nitrogen, starting stirring, raising the temperature to 80 ℃, and carrying out reaction for 3 hours to obtain an intermediate product;
adding 80g of water and 12g of triethylene tetramine into the intermediate product, stirring and mixing uniformly, raising the temperature to 240 ℃, carrying out reaction for 4.0h, drying and removing water from the obtained reaction product to obtain the poly-amino methyl glucoside, wherein the yield is 96.44%.
The poly (aminomethyl) glycoside prepared in example 7 of the present invention has the structure shown in formula 7:
in the formula 7, m is 1-3, and n is 2.
According to the method of the technical scheme, the shale recovery rate once and the shale relative recovery rate of the poly-amino methyl glycoside prepared in the embodiment 7 of the invention rolling for 16 hours at 180 ℃ are tested, and the test results are shown in table 1.
Example 8
Adding 15g of ethyl glucoside, 12g of epoxybutane, 11g of phosphorus pentachloride and 1.5g of dodecylbenzene sulfonic acid into a high-temperature high-pressure reaction kettle, purging air in the kettle by using nitrogen, raising the pressure to 5.0MPa by using the nitrogen, starting stirring, raising the temperature to 80 ℃, and carrying out reaction for 3 hours to obtain an intermediate product;
adding 80g of water and 12g of tetraethylenepentamine into the intermediate product, stirring and mixing uniformly, raising the temperature to 240 ℃, carrying out reaction for 4.0h, drying and removing water from the obtained reaction product to obtain the poly (aminoethyl) glycoside with the yield of 96.68%.
The poly (aminoethyl) glycoside prepared in example 8 of the present invention has the structure shown in formula 8:
in the formula 8, m is 1-3, and n is 3.
According to the method of the technical scheme, the shale recovery rate once and the shale relative recovery rate of the poly-aminoethyl glycoside prepared by the method of the invention in the embodiment 8 are tested after rolling for 16 hours at 180 ℃, and the test results are shown in table 1.
Example 9
Adding 15g of propyl glucoside, 12g of cyclopentane epoxide, 11g of thionyl chloride and 1.6g of sulfamic acid into a high-temperature high-pressure reaction kettle, purging air in the kettle by nitrogen, raising the pressure to 5.0MPa by nitrogen, starting stirring, raising the temperature to 80 ℃, and carrying out reaction for 3 hours to obtain an intermediate product;
adding 90g of water and 12g of pentaethylenehexamine into the intermediate product, stirring and mixing uniformly, raising the temperature to 240 ℃, carrying out reaction for 4.0h, drying and removing water from the obtained reaction product to obtain the poly-aminopropyl glucoside, wherein the yield is 96.89%.
The poly (aminopropyl) glycoside prepared in example 9 of the present invention has the structure shown in formula 9:
in the formula 9, m is 1-3, and n is 4.
According to the method of the technical scheme, the primary recovery rate of shale and the relative recovery rate of shale of the poly (aminopropyl) glucoside prepared in the embodiment 9 of the invention are tested when the poly (aminopropyl glucoside) rolls for 16 hours at 180 ℃ and 300 ℃, and the test results are shown in table 1.
TABLE 1 shale inhibition performance test results of the poly (aminoalkyl glycoside) prepared by the examples of the present invention
| Examples | High temperature rolling condition | Shale primary recovery rate% | Relative recovery of shale,% |
| 1 | 180℃、16h | 95.12 | 98.38 |
| 2 | 180℃、16h | 95.34 | 98.27 |
| 3 | 180℃、16h | 95.78 | 98.47 |
| 4 | 180℃、16h | 96.63 | 98.44 |
| 5 | 180℃、16h | 96.32 | 98.96 |
| 6 | 180℃、16h | 96.10 | 98.56 |
| 7 | 180℃、16h | 95.65 | 98.43 |
| 8 | 180℃、16h | 96.47 | 98.29 |
| 9 | 180℃、16h | 96.81 | 98.64 |
| 9 | 300℃、16h | 93.87 | 99.37 |
TABLE 2 test results of compatibility of the Polyaminomethyl glycoside prepared in example 1 of the present invention with drilling fluids
As can be seen from tables 1 and 2, the aqueous solution of the poly (aminoalkyl) glycoside provided by the invention with the mass concentration of 1% rolls at the high temperature of 180 ℃ for 16h, the primary recovery rate of shale is more than 95%, and the relative recovery rate is more than 98%; hot rolling for 16h at 300 ℃, wherein the once recovery rate of the shale is still more than 90 percent; high-temperature resistance is good. The poly-amino alkyl glycoside prepared by the embodiment of the invention has better shale inhibition performance and high temperature resistance; after 3% of the poly-amino alkyl glycoside prepared by the embodiment of the invention is added into different drilling fluids, the performance of the drilling fluids is not damaged, the flow pattern of the drilling fluids is improved, the viscosity is reduced, the cutting is improved, and the amount of the filtrate invading stratum is reduced.
From the above examples, it can be seen that the present invention provides a poly (aminoalkyl) glycoside having the structure shown in formula I; in the formula I, R1Selected from alkyl with 1-10 carbon atoms; r2Selected from alkyl with 1-5 carbon atoms, m is 1-3, and n is 0-4. The invention provides a preparation method of the poly amino alkyl glycoside in the technical scheme, which comprises the following steps: reacting alkyl glycoside, an alkylene oxide compound, a chlorinating agent and an acid catalyst to obtain an intermediate product; and reacting the intermediate product with water and organic amine to obtain the poly-amino alkyl glycoside. The poly-amino alkyl glycoside provided by the invention has better shale inhibition and high temperature resistance. In addition, the poly-amino alkyl glycoside provided by the invention has better compatibility with drilling fluid. In addition, the preparation method of the poly-amino alkyl glycoside provided by the invention takes natural renewable substances as raw materials, and the prepared product is safe and environment-friendly; in addition, the reaction conditions in the preparation process are mild, the preparation process is simple, water is used as a solvent, and no wastewater, waste gas or waste residue is discharged in the production process.
Claims (7)
1. A method of preparing a poly (aminoalkyl) glycoside, comprising:
reacting alkyl glycoside, an alkylene oxide compound, a chlorinating agent and an acid catalyst to obtain an intermediate product, wherein the alkyl glycoside has a structure shown in a formula II:
in the formula II, R1Selected from alkyl with 1-10 carbon atoms;
the alkylene oxide compound has a structure shown in formula III:
in the formula III, R2Is an alkyl group having 1 to 5 carbon atoms;
reacting the intermediate product with water and organic amine to obtain poly-amino alkyl glycoside, wherein the organic amine has a structure shown in a formula IV:
in the formula IV, n is 0-4;
the reaction temperature of the intermediate product, water and organic amine is 180-240 ℃;
the mass ratio of the alkyl glycoside to the alkylene oxide compound to the water to the acidic catalyst to the chlorinating agent to the organic amine is (10-15): 8-12): 50-90): 0.8-1.6): 9-11): 10-12);
the poly (aminoalkyl-glycoside) has the structure shown in formula I:
in the formula I, R1Selected from alkyl with 1-10 carbon atoms;
R2selected from alkyl with 1-5 carbon atoms;
m is 1-3;
n is 0 to 4.
2. The method of claim 1, wherein the alkyl glycoside is methyl glycoside, ethyl glycoside, propyl glycoside, butyl glycoside, pentyl glycoside, or hexyl glycoside.
3. The process according to claim 1, wherein the alkylene oxide is propylene oxide, butylene oxide or pentylene oxide.
4. The method of claim 1, wherein the acidic catalyst is hydrofluoric acid, hydrochloric acid, sulfuric acid, phosphoric acid, tartaric acid, oxalic acid, p-toluenesulfonic acid, dodecylbenzenesulfonic acid, or sulfamic acid.
5. The process according to claim 1, characterized in that the chlorinating agent is thionyl chloride, sulfuryl chloride, phosphorus trichloride or phosphorus pentachloride.
6. The method of claim 1, wherein the organic amine comprises diethylenetriamine, triethylenetetramine, tetraethylenepentamine, or pentaethylenehexamine.
7. The use of a polyaminoalkyl glycoside in a drilling fluid, the polyaminoalkyl glycoside prepared by the method of claim 1.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201510486574.9A CN106432378B (en) | 2015-08-10 | 2015-08-10 | Polyaminoalkyl glucoside and preparation method and application thereof |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201510486574.9A CN106432378B (en) | 2015-08-10 | 2015-08-10 | Polyaminoalkyl glucoside and preparation method and application thereof |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN106432378A CN106432378A (en) | 2017-02-22 |
| CN106432378B true CN106432378B (en) | 2020-04-24 |
Family
ID=58093454
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN201510486574.9A Active CN106432378B (en) | 2015-08-10 | 2015-08-10 | Polyaminoalkyl glucoside and preparation method and application thereof |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN106432378B (en) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN107090281A (en) * | 2017-05-05 | 2017-08-25 | 辽宁石油化工大学 | A kind of preparation method of drilling fluid mobile phase |
| CN109694697A (en) * | 2017-10-23 | 2019-04-30 | 中石化石油工程技术服务有限公司 | A kind of drilling fluid polyamine shale inhibitor and preparation method thereof and drilling fluid |
| CN111320661A (en) * | 2018-12-13 | 2020-06-23 | 中石化石油工程技术服务有限公司 | Polyamino sulfonated alkyl glycoside, preparation method thereof and drilling fluid |
| CN111320657B (en) * | 2018-12-13 | 2023-02-17 | 中国石油化工集团有限公司 | Silamidoalkyl glycoside, preparation method thereof and drilling fluid |
| CN111320727B (en) | 2018-12-13 | 2022-10-14 | 中国石油化工集团有限公司 | Aryl substituted sugar or glycoside and application thereof in drilling fluid composition |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102766444A (en) * | 2012-08-02 | 2012-11-07 | 中国石油化工股份有限公司 | Drilling fluid inhibitor and preparation method thereof |
| CN104140454A (en) * | 2013-10-29 | 2014-11-12 | 中国石油化工股份有限公司 | Polyether amine based alkyl glycoside for drilling fluid and preparation method thereof |
-
2015
- 2015-08-10 CN CN201510486574.9A patent/CN106432378B/en active Active
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102766444A (en) * | 2012-08-02 | 2012-11-07 | 中国石油化工股份有限公司 | Drilling fluid inhibitor and preparation method thereof |
| CN104140454A (en) * | 2013-10-29 | 2014-11-12 | 中国石油化工股份有限公司 | Polyether amine based alkyl glycoside for drilling fluid and preparation method thereof |
Also Published As
| Publication number | Publication date |
|---|---|
| CN106432378A (en) | 2017-02-22 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CN106432378B (en) | Polyaminoalkyl glucoside and preparation method and application thereof | |
| CN104650823B (en) | Height ooze extra-high ooze reservoir protective material composition and drilling fluid and application thereof | |
| CN111718698B (en) | Hyperbranched polyetheramine environment-friendly shale inhibitor, preparation method thereof and water-based drilling fluid | |
| CN106350036B (en) | A kind of synthetic method of alkyl tetramine, four amine product of alkyl and its shale control agent | |
| CN109694473B (en) | Polyether amine shale inhibitor for drilling fluid, preparation method of polyether amine shale inhibitor and drilling fluid | |
| CN112226216B (en) | High-efficiency petroleum drilling fluid and preparation method thereof | |
| CN104877654A (en) | Compound oil-displacing agent containing asymmetric di-long chain alkylmethyl carboxyl betaine and application thereof | |
| CN106336467B (en) | Modification of chitosan and preparation method thereof and application and drilling fluid and its application as shale control agent | |
| CN106496048B (en) | A kind of alkyl gemini quaternary ammonium salt suitable for shale gas horizontal well | |
| CN103958433A (en) | Cementing composition comprising anionically- and hydrophobically-modified cellulose ethers and its use | |
| CN106281263A (en) | A kind of Ultra-low molecular weight intercalation inhibitor and preparation method thereof | |
| CN107987808A (en) | A kind of drilling fluid | |
| CN109135696B (en) | High-temperature high-density drilling fluid with strong suspension stability and preparation method thereof | |
| CN103272522A (en) | Aromatic group-containing amine oxide type ampholytic surfactant, and preparation method and application thereof | |
| CN110801774B (en) | Preparation method and application of dication temperature-resistant recoverable surfactant | |
| CN106380407B (en) | A kind of Ultra-low molecular weight dendroid alkyl hexamine shale control agent and its synthetic method | |
| CN111763504B (en) | Environment-friendly temperature-resistant ether amine shale inhibitor and water-based drilling fluid prepared from same | |
| CN112812076A (en) | Bis-sulfonic acid-based surfactant, clean fracturing fluid and preparation method thereof | |
| CN106367042B (en) | Modification of chitosan is as the application of shale control agent and the application of temperature resistance environment-friendly type water base drilling fluid | |
| CN104449596B (en) | A kind of polyether polyol shale control agent and its preparation and application | |
| CN110684515B (en) | Substituted sugars or glycosides and their use in drilling fluid compositions | |
| CN113667072A (en) | Preparation method and application of salt-tolerant hydrophobic polymer | |
| CN111320661A (en) | Polyamino sulfonated alkyl glycoside, preparation method thereof and drilling fluid | |
| CN109054798B (en) | Preparation method of high-temperature clay stabilizer for oil field | |
| CN114957126A (en) | Cleanup additive for oilfield acidizing and fracturing and synthetic method thereof |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| C06 | Publication | ||
| PB01 | Publication | ||
| SE01 | Entry into force of request for substantive examination | ||
| SE01 | Entry into force of request for substantive examination | ||
| GR01 | Patent grant | ||
| GR01 | Patent grant |